Martha's Vineyard Rental Homes For Large Groups

Find a wonderful variety of Martha’s Vineyard vacation rentals for large groups and families. Find homes for large groups in Chilmark, Oak Bluffs, Edgartown, and other popular communities on Martha’s Vineyard. Whether you are looking for waterfront views, walking distance to the beach or close to downtown, find your perfect Martha’s Vineyard vacation home here!

Scroll to view Martha's Vineyard vacation rentals below. Contact us today if you would like to learn more about a specific property. Register with the site to save all of your favorite properties and receive email alerts when new listings come onto the market. If you already have an account, feel free to sign in.

 

Rental Price$5,000 to $13,500

Rental ID 137839

  • RTR Vacation Rental
  • Lease $5,000 to $13,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$1,750 to $11,000

Rental ID 137319

  • RTR Vacation Rental
  • Property Name Harbor front home
  • Lease $1,750 to $11,000
  • Village Vineyard Haven
  • Bedrooms 5

Perched high on a sunny bluff, this quintessential Vineyard Haven harbor front home is located on “little Hatch Road” – that sweet little enclave lying midway between West Chop and downtown. Enjoy sweeping views of Vineyard Sound, East Chop and Cape Cod from your spacious, enclosed, heated porch or from the back lawn. From the lawn, mosey down the steps to your 146-foot private beach. The classic house is fully restored, yet preserves much of its vintage charm – buttery hardwood floors, soapstone kitchen sink, paneled butler’s pantry, Old World bathroom fixtures and more. With five bedrooms, two full baths and a delightful attached “bunk house” for the kids, there’s plenty of room for family and friends to spread out and enjoy.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$3,000 to $5,500

Rental ID 136744

  • RTR Vacation Rental
  • Lease $3,000 to $5,500
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 2

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$3,000 to $6,000

Rental ID 136204

  • RTR Vacation Rental
  • Lease $3,000 to $6,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Beautiful home in a perfect location in Oak Bluffs. Fully renovated in 2015 including central A/C and huge deck with pergola! This home is very well kept and lovingly furnished for both style and comfort with a spacious layout for vacations with families and friends. Large two-story, classic Cape Cod style home with 4 Bedrooms and 2 Full Baths, includes large deck, screened porch, outdoor stone patio and furnished basement. Located close enough to the action of Curcuit Avenue in downtown Oak Bluffs, yet tucked away in a quit neighborhood, with easy access to key routes along County and Barnes Roads, this home is secluded by the surrounding forests of the school yards and Trade Winds Field and Trails. The expansive first floor includes a newly remodeled, open-concept kitchen, which opens up to a large great room with dining room and sitting areas and a separate family room with 55 TV. French doors and sliders open up to several, large outdoor areas, including a deck, a screened porch and a stone patio. The doors also allow wonderful island breezes throughout the home. A private bedroom is also located on the first floor, along with a renovated full bathroom. Oak hardwood floors are featured throughout the entire interior of the home. The second floor has 3 bedrooms and a full bath. The basement is furnished as a game room and home theater with a 65 TV and real 10 shuffle board table, as well as DVDs, games, cards and more. Families with children can also enjoy the benefits of Oak Bluffs school playground and tennis courts located adjacent to the property as well. The many beautiful outdoor spaces of the home seem endless. They include a large deck covered with cedar pergola and outdoor dining

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$1,500 to $4,000

Rental ID 135192

  • RTR Vacation Rental
  • Lease $1,500 to $4,000
  • Village West Tisbury
  • Bedrooms 4
  • Bathrooms 2

Live the sea-faring charm of Martha s Vineyard in this appealing, historic Sea Captain s home. Centrally located in West Tisbury village, this country farmhouse was home to members of the White House Staff when President Clinton made MV his "summer white house". The home features an elegant curved staircase in foyer and a "secret" back staircase leading from the kitchen to the master suite. There are 3-4 spacious bedrooms with air conditioners, desks, and sitting areas. There is a grand piano for your enjoyment. The living room has digital cable TV. Adjoining the living room is a separate dining room with a special farm "tavern" table constructed from a ship s starboard hatch cover, and charming country kitchen. Out of doors relax with a drink on the appealing front porch and watch the world go by. There is private rear patio and a charcoal grill. Walk to Alley s General store, café and deli - and you are steps away from the Famous Vineyard Farmers Market. The Sea Captain s home is located near two of most exquisite and unspoiled beaches. Relax at Lambert s Cove Beach or Long Point South Beach.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$2,150 to $4,000

Rental ID 135092

  • RTR Vacation Rental
  • Lease $2,150 to $4,000
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 3

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$3,000 to $6,000

Rental ID 135069

  • RTR Vacation Rental
  • Lease $3,000 to $6,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 1

Leave your worries and your car behind - this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four bedrooms and one and a half baths, offering the perfect juxtaposition of cottage charm and modern beach chic; the style is incredibly livable, comfortable, colorful and relaxed - all vital ingredients to the perfect vacation.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$4,000 to $12,000

Rental ID 134575

  • RTR Vacation Rental
  • Lease $4,000 to $12,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach! The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern, Chilmark Community Center, etc.). It is also a short ride to Menemsha Village (fishing, fish markets, galleries, restaurants, and sunsets on the beach). This 1713 Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to honor its past while embracing today’s contemporary lifestyle. The house is fully air- conditioned and has Wi-Fi, high speed Internet and cable TV. A beautiful three-season porch was added to the back of the house. It is a relaxing place to sit, read, play a game, watch TV, or simply observe what is going on outside. The porch leads to a bluestone patio with a teak dining table with seating for 8 under a market umbrella along with a number of chairs to relax in and a gas grill. Adjacent to the patio is a large private outdoor shower. The house is surrounded by an expansive lawn bordered by stonewalls. The house is remarkably open on the first floor. The porch leads into a fully equipped cook’s kitchen with high-end appliances, quartz countertops and an island with seating. The dining room has a farmer’s table that seats up to 10 along with an additional sitting area by the fireplace. The library/media room is a cozy place to sit and talk, read by the fireplace, or binge watch that show you just never got to last year on a large flat screen TV. The final room downstairs is the first, of two, en suite master bedrooms (queen bed). It has a fireplace, flat screen TV, and a marble and tile bathroom. A French door leads from this bedroom to the bluestone patio. The central hallway contains a half bath and two stairways that lead to the second floor where you will find four additional bedrooms, (two queens, one twin and an en suite king), a full laundry and a large bathroom with an oversized tub/shower. The 2nd floor master bedroom (king bed) has a flat screen TV, an attached walk-in closet and en suite marble and tile bath. High quality linens and towels are provided throughout the house. The real bonus of this house is its key to Hancock Beach—located approximately 1.5 miles from the house down a private road. Hancock Beach is a premier private South Shore ocean beach adjacent to Chilmark Pond so that both can be enjoyed. Tenants can bring kayaks to the pond to explore this beautiful, unspoiled environment. Tenants also have access to Chilmark town beaches—Lucy Vincent and Squibnocket. Beach chairs, towels, umbrellas and coolers are all provided.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$2,990 to $6,990

Rental ID 134518

  • RTR Vacation Rental
  • Lease $2,990 to $6,990
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 4

With sweeping views of Vineyard Haven Harbor, this recently built, in-town luxury home, combines commanding water views with four levels of sophisticated and stylish living space, including two roof top decks, Home Theater, tournament Pool Room, Penthouse Lounge, and more. The main floor of Captain Spring House features an open Great Room designed for entertaining, with Living and Dining Ares, plus a large Gourmet Kitchen. The fully-equipped Chef s Kitchen features marble countertops, grand prep island/breakfast bar with seating for eight, Wolf and Sub Zero stainless appliance, two farmer sinks, double dishwashers, and wine refrigerator. There are hardwood floors and high ceilings throughout the home. All four bedrooms feature full marble baths with tub and shower, and flat screen TVs. The second floor Master Suite also has a glass walk-in shower and whirlpool with harbor views. The third floor Penthouse Lounge features phenomenal views, sectional seating, wet bar, and refrigerators. Best of all, walk out onto two large mahogany sun decks that face the harbor. One has outdoor shower. The lower level features both a Home Theater and a Pool Room Lounge. There is a tournament pool table and a fully-equipped wet bar. Captain Spring House sits quietly on a side street, just steps from downtown Vineyard Haven with its charming Main Street, restaurants, shops, beach, and ferry which is only 2 blocks away.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$6,000 to $8,000

Rental ID 133995

  • RTR Vacation Rental
  • Lease $6,000 to $8,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

This brand new construction located just minutes from downtown Oak Bluffs is well appointed and comfortable. A first floor master outfitted with a king bed and is ADA compliant is perfect for grandparents or the nanny. Upstairs you will find three more bedrooms. A generous sized master with sitting area and en suite bath. Two additional bedrooms that share a lovely bath with double vanity and walk in shower. The living area is open concept with a 65 inch flat screen television and comfortable furnishings for movie night. The kitchen is well appointed with high end pots and pans as well as a kitchen-Aid mixer.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details